This invention relates to a novel 4-phenethylaminopyrimidine derivative which is an agricultural and horticultural chemical for controlling noxious organisms useful as an insecticide, an acaricide, a fungicide and a nematocide.
As a 4-phenethylaminopyrimidine derivative similar to the 4-phenethylaminopyrimidine derivative of the present invention, the following compounds have been known.
(1) In Japanese Provisional Patent Publication No. 176967/1982 (which corresponds to U.S. Pat. No. 4,435,402), it has been described that a compound represented by the following formula: ##STR2## wherein R.sup.1 and R.sup.2 each represent a lower alkyl group or a halogen atom; X represents an alkylene group; and Z represents a substituted or unsubstituted phenyl group (a substituent(s) is/are one or two substituent(s) selected from a halogen, a lower alkyl and a lower alkoxy), a furyl group or a thienyl group; provided that the definitions of R.sup.1 R.sup.2 X and Z are limited only to the above formula, PA1 (2) In Japanese Provisional Patent Publication No. 36666/1984, it has been described that a compound represented by the following formula: ##STR3## wherein R.sup.1 and R.sup.2 each represent a lower alkyl group or a halogen atom, or R.sup.1 and R.sup.2 are combined to represent a trimethylene group or a tetramethylene group; R.sup.3 represents a hydrogen atom or a lower alkyl group; X represents an alkylene group; and Z represents a substituted or unsubstituted phenyl group (a substituent (s) is/are one or two substituent (s) selected from a halogen, a lower alkyl and a lower alkoxy), a furyl group or a thienyl group; provided that the definitions of R.sup.1 to R.sup.3, X and Z are limited only to the above formula, PA1 (3) In Japanese Provisional Patent Publication No. 225364/1988 (which corresponds to U.S. Pat. No. 4,895,849), it has been described that a compound represented by the following formula: ##STR4## wherein R.sup.1 represents a hydrogen atom or a lower alkyl group which is unsubstituted or substituted by a halogen atom; R.sup.2 and R.sup.3 each independently represent a halogen atom or a lower alkyl group which is unsubstituted or substituted by a halogen atom, a lower alkoxy group or a lower alkylthio group; R.sup.4 represents a hydrogen atom, a halogen atom or a lower alkyl group; Q represents a phenyl group or a heterocyclic group, each of which is unsubstituted or substituted by a halogen atom, a nitro group, a lower alkoxy group, a lower alkylthio group, a lower alkyl group which is unsubstituted or substituted by a halogen atom or a lower alkoxy group, a phenyl group which is unsubstituted or substituted by a lower alkoxy group, or a phenoxy group which is unsubstituted or substituted by a halogen atom or a lower alkyl group which is unsubstituted or substituted by a halogen atom; the heterocyclic group may be substituted by an oxo group; A represents a lower alkylene group which is substituted by one or two substituent(s) selected from the group consisting of a cycloalkyl group having 3 to 5 carbon atoms, a lower alkynyl group and a lower alkyl group which is unsubstituted or substituted by a halogen atom, a lower alkoxy group or a lower alkylthio group; and B represents a direct bond, an oxygen atom, a sulfur atom, a straight or branched lower alkylene group or a lower alkyleneoxy group; provided that the definitions of R.sup.1 to R.sup.4 A, B and Q are limited only to the above formula, PA1 (4) In Japanese Provisional Patent Publication No. 68362/1989 (which corresponds to U.S. Pat. No. 4,994,616), it has been described that a compound represented by the following formula: ##STR5## wherein R.sup.1 and R.sup.2 each independently represent a halogen atom or a lower alkyl group; R.sup.3 represents a lower alkyl group or a cycloalkyl group having 3 to 5 carbon atoms; R.sup.4 represents a halogen atom or a lower alkyl group; n represents 0, 1 or 2; and Q represents an alkyl group having 5 to 10 carbon atoms, an allyl group, a geranyl group, a farnesyl group, a lower alkyl group substituted by 1 to 4 halogen atoms, a cycloalkylmethyl group having 3 to 6 carbon atoms, a lower alkoxy group, an ethyl group substituted by a phenoxy group which is substituted by a lower alkoxyalkyl group, a lower alkylthio group, a lower alkylsulfonyl group or 1 or 2 lower alkyl group(s), a glycidyl group, an acetonyl group, a dioxolanylmethyl group substituted by a phenoxymethyl group which may be unsubstituted or substituted by a chlorine atom, a 2,2-diethoxyethyl group, a 1-ethoxycarbonylethyl group, a trimethylsilylmethyl group, a 1-pyridylethyl group, or a lower alkyl group substituted by a benzylimino group which may be substituted by a lower alkoxyimino group or a lower alkyl group; provided that the definitions of R.sup.1 to R.sup.4, Q and n are limited only to the above formula, PA1 (5) In Japanese Provisional Patent Publication No. 7267/1991 (which corresponds to U.S. Pat. No. 5,141,941), it has been described that a compound represented by the following formula: ##STR6## wherein R.sup.1 represents a hydrogen atom, a halogen atom, a halo-lower alkyl group, an alkanoyl group, a nitro group, a cyano group or a 1,3-dioxolan-2-yl group; R.sup.2 and R.sup.3 each represent a halogen atom or a lower alkyl group, or R.sup.2 and R.sup.3 are condensed to a pyrimidine ring with carbon atoms to which they are bonded to represent an unsaturated 5- or 6-membered ring which may have one sulfur atom constituting the ring; R.sup.4 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cycloalkyl group or an amino group which may be substituted by a lower alkoxy group or a lower alkyl group; R.sup.5 represents a hydrogen atom, a lower alkyl group or a cycloalkyl group; and Z represents a carbon atom or a nitrogen atom; provided that the definitions of R.sup.1 to R.sup.5 and Z are limited only to the above formula, PA1 (6) In Japanese Provisional Patent Publication No. 163066/1991 (which corresponds to U.S. Pat. No. 5,141,941), it has been described that a compound represented by the following formula: ##STR7## wherein R.sup.1 represents a hydrogen atom or a halogen atom; R.sup.2 and R.sup.3 each represent a hydrogen atom, a halogen atom or a lower alkyl group, or R.sup.2 and R.sup.3 are condensed to a pyrimidine ring with carbon atoms to which they are bonded to represent a saturated or unsaturated 5- or 6-membered ring which may have one sulfur atom constituting the ring; R.sup.4 represents a hydrogen atom, a halogen atom, a lower alkyl group, a cycloalkyl group, a lower alkoxy group, a lower alkylthio group or an amino group which may be substituted by a lower alkyl group; R.sup.5 represents a hydrogen atom, a lower alkyl group, a cycloalkyl group or a halo-lower alkyl group; R.sup.6 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or a halo-lower alkoxy group; and n represents an integer of 1 or 2; provided that the definitions of R.sup.1 to R.sup.6 and n are limited only to the above formula, PA1 (7) In Japanese Provisional Patent Publication No. 225976/1992, it has been described that a compound represented by the following formula: ##STR8## wherein R.sup.1 represents a hydrogen atom, a lower alkyl group or a halogen atom; R.sup.2 represents a halogen atom; and R.sup.3 represents a lower alkyl group; or R.sup.2 and R.sup.3 are condensed to a pyrimidine ring with carbon atoms to which they are bonded to represent a saturated or unsaturated 5- or 6-membered ring which may have one sulfur atom; R.sup.4 represents a hydrogen atom, a lower alkyl group or a cycloalkyl group; and A represents a methylene group or an ethylene group each of which is substituted by 1 to 4 halogen atoms; provided that the definitions of R.sup.1 to R.sup.4 and A are limited only to the above formula, PA1 (8) In Japanese Provisional Patent Publication No. 201999/1993 (which corresponds to U.S. Pat. No. 5,280,025), it has been described that a compound represented by the following formula: ##STR9## wherein R.sup.1 represents a halogen atom, a lower acyloxy group, a hydroxyl group, a lower alkoxy group or a lower alkylthio group; R.sup.2 represents a lower alkyl group, a hydrogen atom or a cycloalkyl group; R.sup.3 represents a lower haloalkoxy group, a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a lower alkylthio group, a nitro group, a lower haloalkyl group, a lower alkylsulfinyl group, a lower alkylsulfonyl group, a lower haloalkylthio group or a hydroxyl group; and n represents an integer of 1 to 5; provided that the definitions of R.sup.1 to R.sup.3 and n are limited only to the above formula, PA1 R.sup.2 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, `a benzoyl group which is unsubstituted or substituted by at least one of a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms and an alkylthio group having 1 to 4 carbon atoms, PA1 a hydroxyl group, a haloalkylcarbonyl group having 2 to 5 carbon atoms, an alkylsulfonyloxy group having 1 to 4 carbon atoms, a haloalkylsulfonyloxy group having 1 to 4 carbon atoms, an alkylsulfonyl group having 1 to 4 carbon atoms, an alkylsulfinyl group having 1 to 4 carbon atoms, a haloalkylsulfinyl group having 1 to 4 carbon atoms, a tri(C1-4 alkyl)silylalkoxy group having 1 to 4 alkoxy carbon atoms, an alkylthio group having 1 to 4 carbon atoms, PA1 a pyridyloxy group which is unsubstituted or substituted by at least one of a halogen atom and a haloalkyl group having 1 to 4 carbon atoms, PA1 a phenoxy group which is unsubstituted or substituted by at least one of a halogen atom and a haloalkyl group having 1 to 4 carbon atoms, PA1 an alkenyloxy group having 2 to 5 carbon atoms, a haloalkenyloxy group having 2 to 5 carbon atoms, PA1 a benzyl group which is unsubstituted or substituted by at least one of a halogen atom and a hydroxyl group, PA1 a 2-phenyl-2-1,3-dioxolanyl group, an alkoxyiminobenzyl group, a dialkylhydrazonobenzyl group, a nitro group, a haloalkylthio group having 1 to 4 carbon atoms, or an alkynyloxy group having 2 to 5 carbon atoms; PA1 n is an integer of 1 to 5; and PA1 with a 4-.beta.-phenethylamine represented by the following formula (III): ##STR12## wherein R.sup.2 and n have the same meanings as defined above. PA1 (R.sup.1) PA1 (R.sup.2)
is effective for an insecticide, an acaricide and a fungicide.
is effective for an insecticide, an acaricide and a fungicide.
is effective for an insecticide, an acaricide and a fungicide.
is effective for an insecticide, an acaricide and a fungicide.
is effective for a fungicide.
is effective for an insecticide and an acaricide.
is effective for a fungicide.
is effective for an insecticide, an acaricide, a fungicide and a nematocide.
However, there has not been disclosed a 4-.beta.-phenethylamino-pyrimidine derivative in which an ethyl group at 6-position of a pyrimidine ring is substituted as in the present invention.
Thus, the 4-phenethylaminopyrimidine derivative of the present invention is a novel compound and it has not been known that the 4-phenethylaminopyrimidine derivative of the present invention has an activity of controlling noxious organisms for agriculture and horticulture such as an insecticidal, acaricidal, fungicidal or nematocidal activity.